Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email etienne@lcc-toulouse.fr _publ_contact_author_name 'Dr Michel Etienne' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name M.Etienne J.Jaffart F.Maseras J.McGrady M.Reinhold data_CRYSTALS_cif_1 _database_code_CSD 201292 _audit_creation_date 99-05-06 _audit_creation_method CRYSTALS #========================================================================= # 4. TEXT _publ_section_exptl_refinement ; #LIST 12 FULL NB(1, X'S, U'S) UNTIL C(55), H(1, X'S, U[ISO]), H(11, X'S) UNTIL H(32) EQUIV H(11, U[ISO]) UNTIL H(32) END #USE LAST ; _publ_section_references # Add your own references - in alphabetic order ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435 Carruthers, J.R. and Watkin, D.J. (1979), (Chebychev Weighting) Acta Cryst, A35, 698-699 Watkin, D.J., Prout, C.K. Carruthers, R.J. & Betteridge, P. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; #========================================================================== # Now, all the strucure specific goodies #========================================================================== _computing_data_collection ' STOE IPDS ' _computing_cell_refinement ' STOE IPDS ' _computing_data_reduction ; STOE X RED ; _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_melting_point ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' STOE IPDS ' _refine_ls_matrix_type full _refine_ls_weighting_scheme ; w = w'[1-(?F/6?(F))2]2. w' = 1/?(r=1,3)ArTr(x) where Ar are the coefficients for the Chebyshev polynomial Tr(x) with x = Fc/Fc(max) (Carruthers & Watkin, 1979) coef 1.47, -0.132, 0.970 ; _atom_sites_solution_primary SIR92 _atom_sites_solution_hydrogens 'Geometric or located (Fourier difference)' _refine_ls_hydrogen_treatment ; H atoms placed geometrically after each cycle, except H1 to H32 located and refined isotropically with an equivalent Uiso for H11 to H32 ; #************************************************************************** _chemical_name_systematic ; # IUPAC name, in full ? ; _cell_length_a 10.697(2) _cell_angle_alpha 96.58(2) _cell_length_b 10.755(2) _cell_angle_beta 106.87(2) _cell_length_c 13.164(2) _cell_angle_gamma 118.49(2) _cell_volume 1215(1) _symmetry_cell_setting 'Triclinic ' _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'Nb ' -2.1970 0.6210 17.6142 1.1887 12.0144 11.7660 4.0418 0.2048 3.5335 69.7957 3.7559 International_Tables_Vol_IV_Table_2.2B 'Cl ' 0.1320 0.1590 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'B ' 0.0000 0.0010 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 International_Tables_Vol_IV_Table_2.2B 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C22 H33 Nb1 Cl1 N6 B1 ' _chemical_formula_moiety ' C22 H33 Nb1 Cl1 N6 B1 ' _chemical_compound_source ; ? ; _chemical_formula_weight 520.72 _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 24.18 _cell_measurement_temperature 160 _cell_formula_units_Z 2 _exptl_crystal_description ' block ' _exptl_crystal_colour ' orange ' _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 1.42 _exptl_crystal_density_meas ? _exptl_crystal_F_000 535.82 _exptl_absorpt_coefficient_mu 0.63 _exptl_absorpt_correction_type none _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 160 _diffrn_reflns_number 3607 _reflns_number_total 0 _diffrn_reflns_av_R_equivalents 0.00 _reflns_number_observed 3195 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 24.18 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -12 _reflns_limit_h_max 11 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _reflns_observed_criterion >2.00\s(I) _refine_diff_density_min -0.45 _refine_diff_density_max 0.73 _refine_ls_number_reflns 3195 _refine_ls_number_parameters 304 _refine_ls_R_factor_obs 0.0277 _refine_ls_wR_factor_obs 0.0346 _refine_ls_goodness_of_fit_obs 0.9883 _refine_ls_shift/esd_max 0.008596 _refine_ls_structure_factor_coef F _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method 'phi rotation' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type NB1 0.99017(3) 0.20735(2) 0.79696(2) 0.0194 1.0000 Uani CL1 0.92752(7) 0.39838(6) 0.79559(5) 0.0230 1.0000 Uani N1 0.9731(3) -0.0140(2) 0.7544(2) 0.0230 1.0000 Uani N2 0.8359(3) -0.1404(2) 0.6844(2) 0.0219 1.0000 Uani N3 0.7424(3) 0.0527(2) 0.7983(2) 0.0222 1.0000 Uani N4 0.6480(2) -0.0897(2) 0.7268(2) 0.0210 1.0000 Uani N5 0.8452(3) 0.1113(2) 0.6097(2) 0.0225 1.0000 Uani N6 0.7159(2) -0.0294(2) 0.5650(2) 0.0199 1.0000 Uani B1 0.6876(3) -0.1396(3) 0.6336(2) 0.0217 1.0000 Uani C1 1.0604(3) 0.1872(3) 0.9622(2) 0.0267 1.0000 Uani C2 1.2151(4) 0.2651(4) 1.0559(3) 0.0370 1.0000 Uani C3 1.1224(4) 0.3332(4) 1.0492(3) 0.0371 1.0000 Uani C4 1.3432(4) 0.5301(3) 0.9109(3) 0.0408 1.0000 Uani C5 1.2159(3) 0.3792(3) 0.8392(2) 0.0277 1.0000 Uani C6 1.1743(3) 0.2789(3) 0.7492(2) 0.0283 1.0000 Uani C7 1.2311(4) 0.2430(4) 0.6670(3) 0.0449 1.0000 Uani C11 1.2417(4) 0.0522(3) 0.8652(3) 0.0376 1.0000 Uani C12 1.0780(3) -0.0520(3) 0.7856(2) 0.0268 1.0000 Uani C13 1.0078(4) -0.2021(3) 0.7346(2) 0.0290 1.0000 Uani C14 0.8555(3) -0.2559(3) 0.6724(2) 0.0255 1.0000 Uani C15 0.7280(4) -0.4103(3) 0.6051(3) 0.0388 1.0000 Uani C31 0.7343(4) 0.2015(3) 0.9537(3) 0.0384 1.0000 Uani C32 0.6729(3) 0.0628(3) 0.8658(2) 0.0253 1.0000 Uani C33 0.5353(3) -0.0724(3) 0.8390(2) 0.0269 1.0000 Uani C34 0.5231(3) -0.1660(3) 0.7507(2) 0.0242 1.0000 Uani C35 0.3965(3) -0.3229(3) 0.6859(3) 0.0353 1.0000 Uani C51 0.9605(4) 0.3341(3) 0.5446(3) 0.0358 1.0000 Uani C52 0.8414(3) 0.1768(3) 0.5292(2) 0.0255 1.0000 Uani C53 0.7112(3) 0.0791(3) 0.4337(2) 0.0261 1.0000 Uani C54 0.6323(3) -0.0502(3) 0.4587(2) 0.0230 1.0000 Uani C55 0.4807(3) -0.1876(3) 0.3885(2) 0.0308 1.0000 Uani H1 0.591(3) -0.252(3) 0.582(2) 0.021(7) 1.0000 Uiso H11 0.983(4) 0.101(4) 0.974(3) 0.039(4) 1.0000 Uiso H21 1.225(4) 0.222(4) 1.110(3) 0.039(4) 1.0000 Uiso H22 1.300(5) 0.310(4) 1.039(3) 0.039(4) 1.0000 Uiso H31 1.070(4) 0.328(4) 1.103(3) 0.039(4) 1.0000 Uiso H32 1.161(4) 0.420(4) 1.025(3) 0.039(4) 1.0000 Uiso H41 1.4318 0.5582 0.8927 0.0423 1.0000 Uiso H42 1.3700 0.5318 0.9875 0.0423 1.0000 Uiso H43 1.3109 0.5985 0.8993 0.0423 1.0000 Uiso H71 1.3355 0.3223 0.6851 0.0625 1.0000 Uiso H72 1.2284 0.1528 0.6688 0.0625 1.0000 Uiso H73 1.1661 0.2306 0.5939 0.0625 1.0000 Uiso H111 1.2602 0.1496 0.8878 0.0459 1.0000 Uiso H112 1.2610 0.0189 0.9293 0.0459 1.0000 Uiso H113 1.3096 0.0554 0.8298 0.0459 1.0000 Uiso H131 1.0566 -0.2577 0.7415 0.0406 1.0000 Uiso H151 0.7677 -0.4738 0.6081 0.0440 1.0000 Uiso H152 0.6491 -0.4435 0.6344 0.0440 1.0000 Uiso H153 0.6847 -0.4134 0.5293 0.0440 1.0000 Uiso H311 0.8308 0.2784 0.9551 0.0461 1.0000 Uiso H312 0.7503 0.1837 1.0248 0.0461 1.0000 Uiso H313 0.6613 0.2317 0.9377 0.0461 1.0000 Uiso H331 0.4638 -0.0956 0.8748 0.0354 1.0000 Uiso H351 0.3191 -0.3560 0.7166 0.0393 1.0000 Uiso H352 0.4383 -0.3846 0.6899 0.0393 1.0000 Uiso H353 0.3506 -0.3290 0.6096 0.0393 1.0000 Uiso H511 1.0389 0.3770 0.6188 0.0413 1.0000 Uiso H512 1.0070 0.3364 0.4919 0.0413 1.0000 Uiso H513 0.9120 0.3898 0.5330 0.0413 1.0000 Uiso H531 0.6815 0.0977 0.3638 0.0331 1.0000 Uiso H551 0.4424 -0.1780 0.3162 0.0349 1.0000 Uiso H552 0.4931 -0.2705 0.3812 0.0349 1.0000 Uiso H553 0.4085 -0.2034 0.4226 0.0349 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 NB1 0.0205(1) 0.0146(1) 0.0222(1) 0.00487(9) 0.0079(1) 0.0091(1) CL1 0.0264(3) 0.0176(3) 0.0277(3) 0.0052(2) 0.0094(3) 0.0148(3) N1 0.024(1) 0.019(1) 0.026(1) 0.0074(9) 0.010(1) 0.0119(9) N2 0.027(1) 0.017(1) 0.023(1) 0.0061(8) 0.0108(9) 0.0115(9) N3 0.024(1) 0.018(1) 0.023(1) 0.0051(8) 0.010(1) 0.0104(9) N4 0.022(1) 0.018(1) 0.023(1) 0.0076(8) 0.0092(9) 0.0104(9) N5 0.026(1) 0.016(1) 0.025(1) 0.0063(8) 0.011(1) 0.0101(9) N6 0.023(1) 0.015(1) 0.022(1) 0.0057(8) 0.0107(9) 0.0089(9) B1 0.025(1) 0.018(1) 0.023(1) 0.008(1) 0.010(1) 0.011(1) C1 0.026(1) 0.026(1) 0.028(1) 0.010(1) 0.013(1) 0.012(1) C2 0.035(2) 0.038(2) 0.030(2) 0.013(1) 0.008(1) 0.016(1) C3 0.043(2) 0.031(2) 0.030(2) 0.006(1) 0.014(1) 0.015(1) C4 0.033(2) 0.031(2) 0.042(2) 0.009(1) 0.014(1) 0.007(1) C5 0.026(1) 0.022(1) 0.036(1) 0.013(1) 0.013(1) 0.012(1) C6 0.027(1) 0.023(1) 0.040(2) 0.014(1) 0.017(1) 0.014(1) C7 0.054(2) 0.043(2) 0.061(2) 0.024(2) 0.042(2) 0.030(2) C11 0.033(2) 0.035(2) 0.047(2) 0.011(1) 0.011(1) 0.024(1) C12 0.032(1) 0.027(1) 0.030(1) 0.012(1) 0.016(1) 0.020(1) C13 0.040(2) 0.029(1) 0.033(1) 0.012(1) 0.018(1) 0.027(1) C14 0.038(2) 0.021(1) 0.027(1) 0.009(1) 0.017(1) 0.019(1) C15 0.047(2) 0.022(1) 0.047(2) 0.007(1) 0.017(2) 0.020(1) C31 0.044(2) 0.033(2) 0.039(2) 0.004(1) 0.021(2) 0.020(1) C32 0.030(1) 0.028(1) 0.024(1) 0.010(1) 0.012(1) 0.019(1) C33 0.027(1) 0.034(1) 0.028(1) 0.015(1) 0.016(1) 0.019(1) C34 0.024(1) 0.025(1) 0.027(1) 0.014(1) 0.012(1) 0.013(1) C35 0.031(2) 0.029(2) 0.040(2) 0.013(1) 0.017(1) 0.009(1) C51 0.042(2) 0.025(1) 0.038(2) 0.017(1) 0.019(1) 0.013(1) C52 0.035(1) 0.019(1) 0.028(1) 0.010(1) 0.016(1) 0.016(1) C53 0.034(1) 0.027(1) 0.023(1) 0.011(1) 0.012(1) 0.019(1) C54 0.026(1) 0.025(1) 0.023(1) 0.007(1) 0.010(1) 0.017(1) C55 0.029(1) 0.030(1) 0.028(1) 0.007(1) 0.009(1) 0.014(1) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag NB1 . CL1 . 2.4465(6) yes NB1 . N1 . 2.288(2) yes NB1 . N3 . 2.371(2) yes NB1 . N5 . 2.284(2) yes NB1 . C1 . 2.159(3) yes NB1 . C5 . 2.069(3) yes NB1 . C6 . 2.062(3) yes N1 . N2 . 1.370(3) yes N1 . C12 . 1.343(4) yes N2 . B1 . 1.536(4) yes N2 . C14 . 1.355(3) yes N3 . N4 . 1.376(3) yes N3 . C32 . 1.339(4) yes N4 . B1 . 1.529(4) yes N4 . C34 . 1.348(4) yes N5 . N6 . 1.370(3) yes N5 . C52 . 1.339(4) yes N6 . B1 . 1.541(3) yes N6 . C54 . 1.348(3) yes B1 . H1 . 1.09(3) no C1 . C2 . 1.490(4) yes C1 . C3 . 1.539(4) yes C1 . H11 . 0.97(4) no C2 . C3 . 1.478(5) yes C2 . H21 . 0.90(4) no C2 . H22 . 0.91(4) no C3 . H31 . 1.02(4) no C3 . H32 . 0.95(4) no C4 . C5 . 1.475(4) yes C4 . H41 . 0.960(3) no C4 . H42 . 0.960(3) no C4 . H43 . 0.960(4) no C5 . C6 . 1.307(4) yes C6 . C7 . 1.483(5) yes C7 . H71 . 0.960(4) no C7 . H72 . 0.960(3) no C7 . H73 . 0.960(4) no C11 . C12 . 1.488(4) yes C11 . H111 . 0.960(3) no C11 . H112 . 0.960(3) no C11 . H113 . 0.960(3) no C12 . C13 . 1.387(4) yes C13 . C14 . 1.370(4) yes C13 . H131 . 0.960(3) no C14 . C15 . 1.485(4) yes C15 . H151 . 0.960(3) no C15 . H152 . 0.960(4) no C15 . H153 . 0.960(3) no C31 . C32 . 1.491(4) yes C31 . H311 . 0.960(3) no C31 . H312 . 0.960(3) no C31 . H313 . 0.960(3) no C32 . C33 . 1.394(4) yes C33 . C34 . 1.378(4) yes C33 . H331 . 0.960(3) no C34 . C35 . 1.493(4) yes C35 . H351 . 0.960(3) no C35 . H352 . 0.960(3) no C35 . H353 . 0.960(3) no C51 . C52 . 1.498(4) yes C51 . H511 . 0.960(3) no C51 . H512 . 0.960(3) no C51 . H513 . 0.960(3) no C52 . C53 . 1.381(4) yes C53 . C54 . 1.379(4) yes C53 . H531 . 0.960(3) no C54 . C55 . 1.483(4) yes C55 . H551 . 0.960(3) no C55 . H552 . 0.960(3) no C55 . H553 . 0.960(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag CL1 . NB1 . N1 . 162.01(6) yes CL1 . NB1 . N3 . 85.99(5) yes N1 . NB1 . N3 . 82.07(8) yes CL1 . NB1 . N5 . 87.52(5) yes N1 . NB1 . N5 . 77.30(7) yes N3 . NB1 . N5 . 80.53(8) yes CL1 . NB1 . C1 . 110.85(8) yes N1 . NB1 . C1 . 80.53(9) yes N3 . NB1 . C1 . 80.83(9) yes N5 . NB1 . C1 . 152.71(9) yes CL1 . NB1 . C5 . 85.62(8) yes N1 . NB1 . C5 . 109.19(9) yes N3 . NB1 . C5 . 163.1(1) yes N5 . NB1 . C5 . 113.7(1) yes C1 . NB1 . C5 . 88.5(1) yes CL1 . NB1 . C6 . 105.81(7) yes N1 . NB1 . C6 . 82.34(9) yes N3 . NB1 . C6 . 159.94(9) yes N5 . NB1 . C6 . 83.8(1) yes C1 . NB1 . C6 . 108.9(1) yes C5 . NB1 . C6 . 36.9(1) yes NB1 . N1 . N2 . 120.9(2) yes NB1 . N1 . C12 . 132.3(2) yes N2 . N1 . C12 . 106.8(2) yes N1 . N2 . B1 . 121.5(2) yes N1 . N2 . C14 . 109.7(2) yes B1 . N2 . C14 . 128.8(2) yes NB1 . N3 . N4 . 118.9(2) yes NB1 . N3 . C32 . 134.1(2) yes N4 . N3 . C32 . 106.3(2) yes N3 . N4 . B1 . 121.0(2) yes N3 . N4 . C34 . 109.9(2) yes B1 . N4 . C34 . 129.1(2) yes NB1 . N5 . N6 . 120.9(2) yes NB1 . N5 . C52 . 131.2(2) yes N6 . N5 . C52 . 106.4(2) yes N5 . N6 . B1 . 120.4(2) yes N5 . N6 . C54 . 110.1(2) yes B1 . N6 . C54 . 129.5(2) yes N2 . B1 . N4 . 109.6(2) yes N2 . B1 . N6 . 108.8(2) yes N4 . B1 . N6 . 109.0(2) yes N2 . B1 . H1 . 109.7(15) no N4 . B1 . H1 . 108.5(15) no N6 . B1 . H1 . 111.3(15) no NB1 . C1 . C2 . 131.4(2) yes NB1 . C1 . C3 . 109.7(2) yes C2 . C1 . C3 . 58.4(2) yes NB1 . C1 . H11 . 115.2(20) no C2 . C1 . H11 . 112.3(20) no C3 . C1 . H11 . 112.6(21) no C1 . C2 . C3 . 62.5(2) yes C1 . C2 . H21 . 116.8(23) no C3 . C2 . H21 . 117.8(24) no C1 . C2 . H22 . 117.3(22) no C3 . C2 . H22 . 117.7(22) no H21 . C2 . H22 . 114.9(33) no C1 . C3 . C2 . 59.1(2) yes C1 . C3 . H31 . 117.3(19) no C2 . C3 . H31 . 119.6(19) no C1 . C3 . H32 . 115.3(21) no C2 . C3 . H32 . 113.2(22) no H31 . C3 . H32 . 118.6(29) no C5 . C4 . H41 . 109.5(3) no C5 . C4 . H42 . 109.5(3) no H41 . C4 . H42 . 109.5(3) no C5 . C4 . H43 . 109.5(3) no H41 . C4 . H43 . 109.5(3) no H42 . C4 . H43 . 109.5(3) no NB1 . C5 . C4 . 147.0(2) yes NB1 . C5 . C6 . 71.2(2) yes C4 . C5 . C6 . 141.2(3) yes NB1 . C6 . C5 . 71.9(2) yes NB1 . C6 . C7 . 145.4(2) yes C5 . C6 . C7 . 142.7(3) yes C6 . C7 . H71 . 109.5(3) no C6 . C7 . H72 . 109.5(3) no H71 . C7 . H72 . 109.5(4) no C6 . C7 . H73 . 109.5(3) no H71 . C7 . H73 . 109.5(3) no H72 . C7 . H73 . 109.5(4) no C12 . C11 . H111 . 109.5(3) no C12 . C11 . H112 . 109.5(3) no H111 . C11 . H112 . 109.5(3) no C12 . C11 . H113 . 109.5(3) no H111 . C11 . H113 . 109.5(3) no H112 . C11 . H113 . 109.5(3) no N1 . C12 . C11 . 124.3(2) yes N1 . C12 . C13 . 109.2(2) yes C11 . C12 . C13 . 126.5(2) yes C12 . C13 . C14 . 106.9(2) yes C12 . C13 . H131 . 126.5(3) no C14 . C13 . H131 . 126.5(3) no N2 . C14 . C13 . 107.3(2) yes N2 . C14 . C15 . 123.5(3) yes C13 . C14 . C15 . 129.2(2) yes C14 . C15 . H151 . 109.5(3) no C14 . C15 . H152 . 109.5(3) no H151 . C15 . H152 . 109.5(3) no C14 . C15 . H153 . 109.5(3) no H151 . C15 . H153 . 109.5(3) no H152 . C15 . H153 . 109.5(3) no C32 . C31 . H311 . 109.5(3) no C32 . C31 . H312 . 109.5(3) no H311 . C31 . H312 . 109.5(3) no C32 . C31 . H313 . 109.5(3) no H311 . C31 . H313 . 109.5(3) no H312 . C31 . H313 . 109.5(3) no N3 . C32 . C31 . 123.8(3) yes N3 . C32 . C33 . 110.0(2) yes C31 . C32 . C33 . 126.2(3) yes C32 . C33 . C34 . 105.8(3) yes C32 . C33 . H331 . 127.1(3) no C34 . C33 . H331 . 127.1(3) no N4 . C34 . C33 . 107.9(2) yes N4 . C34 . C35 . 122.9(2) yes C33 . C34 . C35 . 129.2(3) yes C34 . C35 . H351 . 109.5(3) no C34 . C35 . H352 . 109.5(3) no H351 . C35 . H352 . 109.5(3) no C34 . C35 . H353 . 109.5(3) no H351 . C35 . H353 . 109.5(3) no H352 . C35 . H353 . 109.5(3) no C52 . C51 . H511 . 109.5(3) no C52 . C51 . H512 . 109.5(3) no H511 . C51 . H512 . 109.5(3) no C52 . C51 . H513 . 109.5(3) no H511 . C51 . H513 . 109.5(3) no H512 . C51 . H513 . 109.5(3) no N5 . C52 . C51 . 123.7(2) yes N5 . C52 . C53 . 109.8(2) yes C51 . C52 . C53 . 126.4(2) yes C52 . C53 . C54 . 106.5(2) yes C52 . C53 . H531 . 126.8(3) no C54 . C53 . H531 . 126.8(3) no N6 . C54 . C53 . 107.2(2) yes N6 . C54 . C55 . 123.8(2) yes C53 . C54 . C55 . 129.0(2) yes C54 . C55 . H551 . 109.5(3) no C54 . C55 . H552 . 109.5(3) no H551 . C55 . H552 . 109.5(3) no C54 . C55 . H553 . 109.5(2) no H551 . C55 . H553 . 109.5(3) no H552 . C55 . H553 . 109.5(3) no #====END data_CRYSTALS_cif _database_code_CSD 201293 _audit_creation_date 99-10-11 _audit_creation_method CRYSTALS # JJ235 IPDS 22-Nov-98 0.71073 #************************************************************************** _publ_section_references # Add your own references - in alphabetic order ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435 Carruthers, J.R. and Watkin, D.J. (1979), (Chebychev Weighting) Acta Cryst, A35, 698-699 Watkin, D.J., Prout, C.K. Carruthers, R.J. & Betteridge, P. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; #========================================================================== _computing_data_collection ' STOE IPDS ' _computing_cell_refinement ' STOE IPDS ' _computing_data_reduction ; STOE X RED ; _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' #========================================================================== _chemical_melting_point ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' STOE IPDS ' _refine_ls_matrix_type full _refine_ls_weighting_scheme ; #LIST 12 FULL NB(1, X'S, U'S) UNTIL C(55), H(1, X'S, U[ISO]) UNTIL H(32) EQUIVALENCE H(1, U[ISO]) UNTIL H(32) END #USE LAST w = w'[1-(?F/6?(F))2]2. w' = 1/?(r=1,3)ArTr(x) where Ar are the coefficients for the Chebyshev polynomial Tr(x) with x = Fc/Fc(max) (Carruthers & Watkin, 1979) coef 2.02 -2.32 1.18 -0.727 -0.114 ; _atom_sites_solution_primary 'Direct_Methods SIR92' _atom_sites_solution_hydrogens 'Geometric or located (Fourier difference)' _refine_ls_hydrogen_treatment ; H atoms placed geometrically after each cycle, except H1 to H32 located and refined isotropically with an equivalent Uiso ; #************************************************************************** _chemical_name_systematic ; # IUPAC name, in full ? ; _cell_length_a 10.747(2) _cell_angle_alpha 96.16(2) _cell_length_b 10.852(2) _cell_angle_beta 106.91(2) _cell_length_c 13.211(2) _cell_angle_gamma 119.21(2) _cell_volume 1228(1) _symmetry_cell_setting 'Triclinic ' _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'Nb ' -2.1970 0.6210 17.6142 1.1887 12.0144 11.7660 4.0418 0.2048 3.5335 69.7957 3.7559 International_Tables_Vol_IV_Table_2.2B 'Br ' -0.3740 2.4560 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'B ' 0.0000 0.0010 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 International_Tables_Vol_IV_Table_2.2B 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C22 H33 Nb1 Br1 N6 B1 ' _chemical_formula_moiety ' C22 H33 Nb1 Br1 N6 B1 ' _chemical_compound_source ; ? ; _chemical_formula_weight 565.17 _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 24.15 _cell_measurement_temperature 160 _cell_formula_units_Z 2 _exptl_crystal_description ' block ' _exptl_crystal_colour ' orange ' _exptl_crystal_size_min 0.37 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 1.53 _exptl_crystal_density_meas ? _exptl_crystal_F_000 570.83 _exptl_absorpt_coefficient_mu 2.10 _exptl_absorpt_correction_type none _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 160 _diffrn_reflns_number 7205 _reflns_number_total 7205 _diffrn_reflns_av_R_equivalents 0.00 _reflns_number_observed 5785 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 0.00 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min -15 _reflns_limit_l_max 15 _reflns_observed_criterion >3.00\?(I) _refine_diff_density_min -2.11 _refine_diff_density_max 1.31 _refine_ls_number_reflns 5785 _refine_ls_number_parameters 299 _refine_ls_R_factor_obs 0.0393 _refine_ls_wR_factor_obs 0.0316 _refine_ls_goodness_of_fit_obs 1.0936 _refine_ls_shift/esd_max 0.000349 _refine_ls_structure_factor_coef F _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method 'phi rotation' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type NB1 -0.00644(3) 0.20766(3) -0.20265(2) 0.0215 1.0000 Uani BR1 -0.06716(5) 0.40949(4) -0.20434(3) 0.0423 1.0000 Uani N1 -0.0259(3) -0.0121(3) -0.2441(2) 0.0232 1.0000 Uani N2 -0.1641(3) -0.1380(3) -0.3147(2) 0.0237 1.0000 Uani N3 -0.2553(3) 0.0540(3) -0.2021(2) 0.0268 1.0000 Uani N4 -0.3522(3) -0.0885(3) -0.2735(2) 0.0233 1.0000 Uani N5 -0.1499(3) 0.1133(3) -0.3895(2) 0.0262 1.0000 Uani N6 -0.2812(3) -0.0267(3) -0.4339(2) 0.0219 1.0000 Uani B1 -0.3112(4) -0.1373(4) -0.3660(3) 0.0234 1.0000 Uani C1 0.0621(4) 0.1857(4) -0.0376(3) 0.0328 1.0000 Uani C2 0.2147(5) 0.2627(5) 0.0552(3) 0.0425 1.0000 Uani C3 0.1240(5) 0.3295(4) 0.0484(3) 0.0431 1.0000 Uani C4 0.2401(6) 0.2479(5) -0.3271(4) 0.0554 1.0000 Uani C5 0.1806(4) 0.2816(4) -0.2470(3) 0.0327 1.0000 Uani C6 0.2188(4) 0.3803(4) -0.1597(3) 0.0300 1.0000 Uani C7 0.3468(5) 0.5344(4) -0.0866(3) 0.0450 1.0000 Uani C11 0.0773(4) -0.0508(4) -0.2137(3) 0.0297 1.0000 Uani C12 0.0052(4) -0.2003(4) -0.2646(3) 0.0308 1.0000 Uani C13 -0.1461(4) -0.2531(3) -0.3267(3) 0.0274 1.0000 Uani C14 0.2432(5) 0.0532(4) -0.1340(3) 0.0417 1.0000 Uani C15 -0.2750(5) -0.4077(4) -0.3944(3) 0.0410 1.0000 Uani C31 -0.3270(4) 0.0625(4) -0.1352(3) 0.0290 1.0000 Uani C32 -0.4652(4) -0.0718(4) -0.1632(3) 0.0313 1.0000 Uani C33 -0.4778(4) -0.1645(4) -0.2509(3) 0.0281 1.0000 Uani C34 -0.2641(5) 0.2002(4) -0.0473(3) 0.0435 1.0000 Uani C35 -0.6057(5) -0.3210(4) -0.3157(3) 0.0395 1.0000 Uani C51 -0.1517(4) 0.1779(3) -0.4705(3) 0.0295 1.0000 Uani C52 -0.2827(4) 0.0806(3) -0.5649(3) 0.0290 1.0000 Uani C53 -0.3642(4) -0.0480(3) -0.5398(2) 0.0262 1.0000 Uani C54 -0.0305(5) 0.3342(4) -0.4562(3) 0.0384 1.0000 Uani C55 -0.5177(4) -0.1849(4) -0.6101(3) 0.0345 1.0000 Uani H1 -0.409(5) -0.249(4) -0.422(3) 0.043(4) 1.0000 Uiso H10 -0.014(5) 0.101(4) -0.026(3) 0.043(4) 1.0000 Uiso H21 0.287(5) 0.302(4) 0.041(4) 0.043(4) 1.0000 Uiso H22 0.213(5) 0.213(4) 0.104(3) 0.043(4) 1.0000 Uiso H31 0.168(5) 0.422(4) 0.032(3) 0.043(4) 1.0000 Uiso H32 0.069(5) 0.328(4) 0.100(3) 0.043(4) 1.0000 Uiso H41 0.1607 0.1534 -0.3809 0.0781 1.0000 Uiso H42 0.2688 0.3229 -0.3639 0.0781 1.0000 Uiso H43 0.3292 0.2455 -0.2883 0.0781 1.0000 Uiso H71 0.4369 0.5646 -0.1032 0.0430 1.0000 Uiso H72 0.3135 0.6008 -0.0997 0.0430 1.0000 Uiso H73 0.3719 0.5361 -0.0104 0.0430 1.0000 Uiso H121 0.0527 -0.2561 -0.2575 0.0432 1.0000 Uiso H141 0.2634 0.1504 -0.1111 0.0496 1.0000 Uiso H142 0.3105 0.0563 -0.1695 0.0496 1.0000 Uiso H143 0.2618 0.0195 -0.0703 0.0496 1.0000 Uiso H151 -0.2359 -0.4707 -0.3911 0.0463 1.0000 Uiso H152 -0.3174 -0.4103 -0.4700 0.0463 1.0000 Uiso H153 -0.3547 -0.4416 -0.3658 0.0463 1.0000 Uiso H321 -0.5376 -0.0955 -0.1284 0.0414 1.0000 Uiso H341 -0.3331 0.1816 -0.0100 0.0542 1.0000 Uiso H342 -0.2549 0.2771 -0.0804 0.0542 1.0000 Uiso H343 -0.1637 0.2304 0.0051 0.0542 1.0000 Uiso H351 -0.6840 -0.3542 -0.2859 0.0430 1.0000 Uiso H352 -0.6504 -0.3269 -0.3919 0.0430 1.0000 Uiso H353 -0.5648 -0.3826 -0.3111 0.0430 1.0000 Uiso H521 -0.3117 0.0989 -0.6348 0.0357 1.0000 Uiso H541 -0.0552 0.3567 -0.5248 0.0413 1.0000 Uiso H542 0.0690 0.3462 -0.4350 0.0413 1.0000 Uiso H543 -0.0277 0.4001 -0.3995 0.0413 1.0000 Uiso H551 -0.5548 -0.1750 -0.6823 0.0366 1.0000 Uiso H552 -0.5072 -0.2679 -0.6169 0.0366 1.0000 Uiso H553 -0.5901 -0.1999 -0.5766 0.0366 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 NB1 0.0207(2) 0.0171(1) 0.0233(1) 0.0041(1) 0.0055(1) 0.0101(1) BR1 0.0444(3) 0.0336(2) 0.0475(2) 0.0079(2) 0.0112(2) 0.0250(2) N1 0.023(2) 0.021(1) 0.024(1) 0.007(1) 0.008(1) 0.012(1) N2 0.029(2) 0.021(1) 0.024(1) 0.009(1) 0.012(1) 0.014(1) N3 0.028(2) 0.025(1) 0.026(1) 0.006(1) 0.010(1) 0.015(1) N4 0.025(2) 0.020(1) 0.023(1) 0.007(1) 0.008(1) 0.012(1) N5 0.028(2) 0.017(1) 0.029(1) 0.009(1) 0.009(1) 0.010(1) N6 0.021(2) 0.021(1) 0.024(1) 0.007(1) 0.009(1) 0.011(1) B1 0.025(2) 0.018(2) 0.024(2) 0.006(1) 0.007(1) 0.011(2) C1 0.033(2) 0.031(2) 0.038(2) 0.012(2) 0.017(2) 0.018(2) C2 0.037(3) 0.049(2) 0.037(2) 0.017(2) 0.011(2) 0.021(2) C3 0.051(3) 0.041(2) 0.035(2) 0.011(2) 0.017(2) 0.023(2) C4 0.066(3) 0.053(3) 0.078(3) 0.032(2) 0.049(3) 0.041(3) C5 0.029(2) 0.029(2) 0.046(2) 0.016(2) 0.017(2) 0.017(2) C6 0.026(2) 0.028(2) 0.035(2) 0.012(1) 0.009(1) 0.015(2) C7 0.029(2) 0.031(2) 0.051(2) 0.011(2) 0.010(2) 0.004(2) C11 0.031(2) 0.032(2) 0.031(2) 0.011(1) 0.013(1) 0.020(2) C12 0.043(2) 0.030(2) 0.036(2) 0.015(1) 0.019(2) 0.028(2) C13 0.040(2) 0.023(2) 0.028(2) 0.011(1) 0.018(2) 0.020(2) C14 0.031(2) 0.042(2) 0.054(2) 0.011(2) 0.008(2) 0.027(2) C15 0.048(3) 0.023(2) 0.051(2) 0.007(2) 0.016(2) 0.022(2) C31 0.031(2) 0.035(2) 0.027(2) 0.011(1) 0.011(1) 0.022(2) C32 0.033(2) 0.040(2) 0.031(2) 0.017(2) 0.017(2) 0.023(2) C33 0.028(2) 0.030(2) 0.030(2) 0.016(1) 0.011(1) 0.017(2) C34 0.051(3) 0.040(2) 0.044(2) 0.004(2) 0.024(2) 0.027(2) C35 0.033(2) 0.031(2) 0.045(2) 0.011(2) 0.017(2) 0.010(2) C51 0.040(2) 0.024(2) 0.032(2) 0.013(1) 0.018(2) 0.019(2) C52 0.035(2) 0.029(2) 0.027(2) 0.013(1) 0.011(1) 0.019(2) C53 0.032(2) 0.029(2) 0.022(2) 0.008(1) 0.009(1) 0.020(2) C54 0.042(3) 0.024(2) 0.040(2) 0.014(1) 0.015(2) 0.012(2) C55 0.028(2) 0.034(2) 0.031(2) 0.006(1) 0.007(1) 0.012(2) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag NB1 . BR1 . 2.5730(4) yes NB1 . N1 . 2.280(2) yes NB1 . N3 . 2.366(3) yes NB1 . N5 . 2.285(3) yes NB1 . C1 . 2.169(4) yes NB1 . C5 . 2.059(4) yes NB1 . C6 . 2.058(3) yes N1 . N2 . 1.373(4) yes N1 . C11 . 1.342(4) yes N2 . B1 . 1.532(5) yes N2 . C13 . 1.354(4) yes N3 . N4 . 1.382(3) yes N3 . C31 . 1.353(4) yes N4 . B1 . 1.540(4) yes N4 . C33 . 1.339(4) yes N5 . N6 . 1.371(4) yes N5 . C51 . 1.341(4) yes N6 . B1 . 1.539(4) yes N6 . C53 . 1.344(4) yes B1 . H1 . 1.11(4) no C1 . C2 . 1.471(5) yes C1 . C3 . 1.528(5) yes C1 . H10 . 0.95(4) no C2 . C3 . 1.462(6) yes C2 . H21 . 0.77(4) no C2 . H22 . 0.88(4) no C3 . H31 . 0.96(4) no C3 . H32 . 1.02(4) no C4 . C5 . 1.483(5) yes C4 . H41 . 0.960(5) no C4 . H42 . 0.960(4) no C4 . H43 . 0.960(5) no C5 . C6 . 1.294(5) yes C6 . C7 . 1.502(5) yes C7 . H71 . 0.960(4) no C7 . H72 . 0.960(4) no C7 . H73 . 0.960(4) no C11 . C12 . 1.386(5) yes C11 . C14 . 1.500(5) yes C12 . C13 . 1.364(5) yes C12 . H121 . 0.960(3) no C13 . C15 . 1.491(5) yes C14 . H141 . 0.960(4) no C14 . H142 . 0.960(4) no C14 . H143 . 0.960(4) no C15 . H151 . 0.960(3) no C15 . H152 . 0.960(4) no C15 . H153 . 0.960(4) no C31 . C32 . 1.385(5) yes C31 . C34 . 1.491(5) yes C32 . C33 . 1.378(4) yes C32 . H321 . 0.960(3) no C33 . C35 . 1.494(5) yes C34 . H341 . 0.960(4) no C34 . H342 . 0.960(4) no C34 . H343 . 0.960(4) no C35 . H351 . 0.960(4) no C35 . H352 . 0.960(4) no C35 . H353 . 0.960(4) no C51 . C52 . 1.377(5) yes C51 . C54 . 1.497(5) yes C52 . C53 . 1.378(4) yes C52 . H521 . 0.960(3) no C53 . C55 . 1.487(5) yes C54 . H541 . 0.960(4) no C54 . H542 . 0.960(4) no C54 . H543 . 0.960(4) no C55 . H551 . 0.960(3) no C55 . H552 . 0.960(3) no C55 . H553 . 0.960(4) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag BR1 . NB1 . N1 . 162.46(7) yes BR1 . NB1 . N3 . 86.24(6) yes N1 . NB1 . N3 . 82.26(9) yes BR1 . NB1 . N5 . 87.66(6) yes N1 . NB1 . N5 . 77.49(9) yes N3 . NB1 . N5 . 80.81(9) yes BR1 . NB1 . C1 . 111.09(9) yes N1 . NB1 . C1 . 80.1(1) yes N3 . NB1 . C1 . 80.8(1) yes N5 . NB1 . C1 . 152.7(1) yes BR1 . NB1 . C5 . 105.26(9) yes N1 . NB1 . C5 . 82.8(1) yes N3 . NB1 . C5 . 160.9(1) yes N5 . NB1 . C5 . 84.4(1) yes C1 . NB1 . C5 . 108.2(1) yes BR1 . NB1 . C6 . 84.43(9) yes N1 . NB1 . C6 . 109.9(1) yes N3 . NB1 . C6 . 162.4(1) yes N5 . NB1 . C6 . 113.6(1) yes C1 . NB1 . C6 . 88.7(1) yes C5 . NB1 . C6 . 36.6(1) yes NB1 . N1 . N2 . 120.7(2) yes NB1 . N1 . C11 . 132.8(2) yes N2 . N1 . C11 . 106.5(2) yes N1 . N2 . B1 . 121.6(2) yes N1 . N2 . C13 . 109.7(3) yes B1 . N2 . C13 . 128.7(3) yes NB1 . N3 . N4 . 119.1(2) yes NB1 . N3 . C31 . 134.8(2) yes N4 . N3 . C31 . 105.4(3) yes N3 . N4 . B1 . 120.2(3) yes N3 . N4 . C33 . 110.5(3) yes B1 . N4 . C33 . 129.2(3) yes NB1 . N5 . N6 . 120.5(2) yes NB1 . N5 . C51 . 131.9(2) yes N6 . N5 . C51 . 106.2(2) yes N5 . N6 . B1 . 120.5(2) yes N5 . N6 . C53 . 110.4(2) yes B1 . N6 . C53 . 129.1(3) yes N2 . B1 . N4 . 109.7(2) yes N2 . B1 . N6 . 109.1(3) yes N4 . B1 . N6 . 108.8(2) yes N2 . B1 . H1 . 110.0(19) no N4 . B1 . H1 . 110.4(20) no N6 . B1 . H1 . 108.7(19) no NB1 . C1 . C2 . 131.3(3) yes NB1 . C1 . C3 . 109.6(2) yes C2 . C1 . C3 . 58.3(3) yes NB1 . C1 . H10 . 115.8(24) no C2 . C1 . H10 . 111.9(24) no C3 . C1 . H10 . 112.3(23) no C1 . C2 . C3 . 62.8(3) yes C1 . C2 . H21 . 116.6(34) no C3 . C2 . H21 . 117.2(32) no C1 . C2 . H22 . 110.8(26) no C3 . C2 . H22 . 115.4(26) no H21 . C2 . H22 . 120.4(42) no C1 . C3 . C2 . 58.9(3) yes C1 . C3 . H31 . 120.5(23) no C2 . C3 . H31 . 114.3(24) no C1 . C3 . H32 . 119.1(21) no C2 . C3 . H32 . 123.5(22) no H31 . C3 . H32 . 111.5(30) no C5 . C4 . H41 . 109.5(4) no C5 . C4 . H42 . 109.5(3) no H41 . C4 . H42 . 109.5(5) no C5 . C4 . H43 . 109.5(4) no H41 . C4 . H43 . 109.5(4) no H42 . C4 . H43 . 109.5(5) no NB1 . C5 . C4 . 145.4(3) yes NB1 . C5 . C6 . 71.6(2) yes C4 . C5 . C6 . 142.9(4) yes NB1 . C6 . C5 . 71.7(2) yes NB1 . C6 . C7 . 146.4(3) yes C5 . C6 . C7 . 141.4(4) yes C6 . C7 . H71 . 109.5(4) no C6 . C7 . H72 . 109.5(4) no H71 . C7 . H72 . 109.5(4) no C6 . C7 . H73 . 109.5(3) no H71 . C7 . H73 . 109.5(4) no H72 . C7 . H73 . 109.5(4) no N1 . C11 . C12 . 109.5(3) yes N1 . C11 . C14 . 124.2(3) yes C12 . C11 . C14 . 126.4(3) yes C11 . C12 . C13 . 106.9(3) yes C11 . C12 . H121 . 126.6(4) no C13 . C12 . H121 . 126.6(3) no N2 . C13 . C12 . 107.5(3) yes N2 . C13 . C15 . 123.7(3) yes C12 . C13 . C15 . 128.7(3) yes C11 . C14 . H141 . 109.5(3) no C11 . C14 . H142 . 109.5(3) no H141 . C14 . H142 . 109.5(4) no C11 . C14 . H143 . 109.5(4) no H141 . C14 . H143 . 109.5(4) no H142 . C14 . H143 . 109.5(3) no C13 . C15 . H151 . 109.5(4) no C13 . C15 . H152 . 109.5(3) no H151 . C15 . H152 . 109.5(4) no C13 . C15 . H153 . 109.5(3) no H151 . C15 . H153 . 109.5(4) no H152 . C15 . H153 . 109.5(4) no N3 . C31 . C32 . 110.1(3) yes N3 . C31 . C34 . 123.3(3) yes C32 . C31 . C34 . 126.6(3) yes C31 . C32 . C33 . 106.3(3) yes C31 . C32 . H321 . 126.9(3) no C33 . C32 . H321 . 126.9(4) no N4 . C33 . C32 . 107.8(3) yes N4 . C33 . C35 . 123.0(3) yes C32 . C33 . C35 . 129.2(3) yes C31 . C34 . H341 . 109.5(4) no C31 . C34 . H342 . 109.5(3) no H341 . C34 . H342 . 109.5(4) no C31 . C34 . H343 . 109.5(3) no H341 . C34 . H343 . 109.5(4) no H342 . C34 . H343 . 109.5(4) no C33 . C35 . H351 . 109.5(3) no C33 . C35 . H352 . 109.5(3) no H351 . C35 . H352 . 109.5(4) no C33 . C35 . H353 . 109.5(3) no H351 . C35 . H353 . 109.5(3) no H352 . C35 . H353 . 109.5(4) no N5 . C51 . C52 . 109.6(3) yes N5 . C51 . C54 . 123.9(3) yes C52 . C51 . C54 . 126.5(3) yes C51 . C52 . C53 . 106.9(3) yes C51 . C52 . H521 . 126.5(3) no C53 . C52 . H521 . 126.6(3) no N6 . C53 . C52 . 106.9(3) yes N6 . C53 . C55 . 124.2(3) yes C52 . C53 . C55 . 128.9(3) yes C51 . C54 . H541 . 109.5(3) no C51 . C54 . H542 . 109.5(3) no H541 . C54 . H542 . 109.5(4) no C51 . C54 . H543 . 109.5(3) no H541 . C54 . H543 . 109.5(3) no H542 . C54 . H543 . 109.5(4) no C53 . C55 . H551 . 109.5(3) no C53 . C55 . H552 . 109.5(3) no H551 . C55 . H552 . 109.5(3) no C53 . C55 . H553 . 109.5(3) no H551 . C55 . H553 . 109.5(4) no H552 . C55 . H553 . 109.5(3) no